P
US4064139AExpiredUtilityPatentIndex 82

Substituted 9,10-dihydroanthracen-9,10-imines

Assignee: MERCK & CO INCPriority: Apr 7, 1975Filed: Oct 28, 1976Granted: Dec 20, 1977
Est. expiryApr 7, 1995(expired)· nominal 20-yr term from priority
Inventors:ANDERSON PAUL SCHRISTY MARCIA EPONTICELLO GERALD S
C07D 471/18C07D 487/08
82
PatentIndex Score
25
Cited by
7
References
55
Claims

Abstract

Substituted 9,10-dihydroanthracen-9,10-imines are disclosed to be minor tranquilizers, anticonvulsnts, muscle relaxants, and to be useful in the treatment of extrapyramidal disorders such as Parkinson's disease; also disclosed are processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. A compound selected from the group consisting of: 2-bromo-11-methyl-9,10-dihydroanthracen-9,10-imine;   2-methoxy-11-methyl-9,10-dihydroanthracen-9,10-imine;   9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine;   2-chloro-11-propyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine;   2-iodo-11-propyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine;   2-bromo-11-propyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine;   2-chloro-11-cyclopropyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine;   2-iodo-11-cyclopropyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine;   2-bromo-11-cyclopropyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine;   2-chloro-11-(3-hydroxypropyl)-9,10-diethyl-9,10-dihydroanthracen-9,10-imine   2-iodo-11-(3-hydroxypropyl)-9,10-diethyl-9,10-dihydroanthracen-9,10-imine;   2-bromo-11-(3-hydroxypropyl)-9,10-diethyl-9,10-dihydroanthracen-9,10-imine;   9,10-dihydro-2,11-dimethyl-9,10-diethylanthracen-9,10-imine;   2-chloro-9,10-dihydro-9,10-diethyl-11-methylanthracen-9,10-imine;   9,10-dihydro-1-fluoro-9,10-diethyl-11-methylanthracen-9,10-imine;   9,10-dihydro-2-methoxy-9,10-diethyl-11-methylanthracen-9,10-imine;   9,10-dihydro-9,10-diethyl-1,11-dimethylanthracen-9,10-imine;   9,10-dihydro-2-trifluoromethyl-9,10-diethyl-11-methylanthracen-9,10-imine;   
     
     
       9. 10-dihydro-2-fluoro-9,10-diethyl-11-methylanthracen-9,10-imine; 2-bromo-9,10-dihydro-9,10-diethyl-11-methylanthracen-9,10-imine;   2-cyano-9,10-dihydro-9,10-diethyl-11-methylanthracen-9,10-imine;   2-methylthio-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine;   1-isopropyl-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine;   2-isopropyl-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine;   2-(N,N-dimethylsulfamoyl)-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine;   2-diethoxymethyl-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine;   11-benzyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine;   10-ethyl-9,11-dimethyl-9,10-dihydroanthracen-9,10-imine;   11-benzyl-2,9-dimethyl-10-ethyl-9,10-dihydroanthracen-9,10-imine;   11-(3-hydroxypropyl)-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine;   11-propyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine;   11-butyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine;   1-chloro-9,11-dimethyl-10-ethyl-9,10-dihydroanthracen-9,10-imine;   11-allyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine;   11-cyclopropylmethyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine;   11-(3-dimethylaminopropyl)-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine;   2-iodo-11-(3-dimethylaminopropyl)-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine;   2-bromo-11-(3-dimethylaminopropyl)-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine;   9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine;   10-vinyl-9,11-dimethyl-9,10-dihydroanthracen-9,10-imine;   2-methoxy-9,11-dimethyl-10-ethyl-9,10-dihydroanthracen-9,10-imine;   2-bromo-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine;   2-nitro-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine;   2-amino-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine;   3,9,11-trimethyl-9,10-dihydroanthracen-9,10-imine;   2,9,11-trimethyl-9,10-dihydroanthracen-9,10-imine;   2-chloro-9,11-dimethyl-9,10-dihydroanthracen-9,10-imine;   9,11-dimethyl-9,10-dihydroanthracen-9,10-imine;   9,11-dimethyl-10-ethyl-9,10-dihydroanthracen-9,10-imine;   9,10-bis(trifluoromethyl)-11-methyl-9,10-dihydroanthracen-9,10-imine;   11-methyl-9,10-dipropyl-9,10-dihydroanthracen-9,10-imine;   11-methyl-9-ethyl-10-propyl-9,10-dihydroanthracen-9,10-imine;   2-carboxaldehyde-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine; and   9,10,11-triethyl-9,10-dihydroanthracen-9,10-imine.   
     
     
       2. 2-Bromo-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       3. 2-Methoxy-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       4. 9,10-Diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       5. 2-Chloro-11-propyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       6. 2-Iodo-11-propyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       7. 2-Bromo-11-propyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       8. 2-Chloro-11-cyclopropyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       9. 2-Iodo-11-cyclopropyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       10. 2-Bromo-11-cyclopropyl-9,10-diethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       11. 2-Chloro-11-(3-hydroxypropyl)-9,10-diethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       12. 2-Iodo-11-(3-hydroxypropyl)-9,10-diethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       13. 2-Bromo-11-(3-hydroxypropyl)-9,10-diethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       14. 9,10-Dihydro-2,11-dimethyl-9,10-diethyl-anthracen-9,10-imine according to claim 1. 
     
     
       15. 2-Chloro-9,10-dihydro-9,10-diethyl-11-methylanthracen-9,10-imine according to claim 1. 
     
     
       16. 9,10-Dihydro-1-fluoro-9,10-diethyl-11-methylanthracen-9,10-imine according to claim 1. 
     
     
       17. 9,10-Dihydro-2-methoxy-9,10-diethyl-11-methylanthracen-9,10-imine according to claim 1. 
     
     
       18. 9,10-Dihydro-9,10-diethyl-1,11-dimethyl-anthracen-9,10-imine according to claim 1. 
     
     
       19. 9,10-dihydro-2-trifluoromethyl-9,10-diethyl-11-methylanthracen-9,10-imine according to claim 1. 
     
     
       20. 9,10-Dihydro-2-fluoro-9,10-diethyl-11-methylanthracen-9,10-imine according to claim 1. 
     
     
       21. 2-Bromo-9,10-dihydro-9,10-diethyl-11-methylanthracen-9,10-imine according to claim 1. 
     
     
       22. 2-Cyano-9,10-dihydro-9,10-diethyl-11-methyl-anthracen-9,10-imine according to claim 1. 
     
     
       23. 2-Methylthio-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       24. 1-Isopropyl-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       25. 2-Isopropyl-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       26. 2-(N,N-Dimethylsulfamoyl)-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       27. 2-Diethoxymethyl-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       28. 11-Benzyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       29. 10-Ethyl-9,11-dimethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       30. 11-Benzyl-2,9-dimethyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       31. 11-(3-Hydroxypropyl)-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       32. 11-Propyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       33. 11-Butyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       34. 1-Chloro-9,11-dimethyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       35. 11-Allyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       36. 11-Cyclopropylmethyl-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       37. 11-(3-Dimethylaminopropyl)-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       38. 2-Iodo-11-(3-dimethylaminopropyl)-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       39. 2-Bromo-11-(3-dimethylaminopropyl)-9-methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       40. 9-Methyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       41. 10-Vinyl-9,11-dimethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       42. 2-Methoxy-9,11-dimethyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       43. 2-Bromo-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       44. 2-Nitro-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       45. 2-Amino-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       46. 3,9,11-Trimethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       47. 2,9,11-Trimethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       48. 2-Chloro-9,11-dimethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       49. 9,11-Dimethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       50. 9,11-Dimethyl-10-ethyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       51. 9,10-Bis(trifluoromethyl)-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       52. 11-Methyl-9,10-dipropyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       53. 11-Methyl-9-ethyl-10-propyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       54. 2-Carboxaldehyde-9,10-diethyl-11-methyl-9,10-dihydroanthracen-9,10-imine according to claim 1. 
     
     
       55. 9,10,11-Triethyl-9,10-dihydroanthracen-9,10-imine according to claim 1.

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